When Jen invites her boss, Paul, and his wife over to dinner to impress him, she and Greg can't remember his wife's name and scramble to avoid embarrassment. Also, Tim urges Tyler to start dating; Matt ends up having a nightmare about parenting after he and Colleen discuss having children; and Joan grows increasingly stressed about Heather living with her.

When Heather finds a map to a time capsule she buried with her brothers as kids, they all set out to find it and dig it up. Also, Jen learns she has a low car service rating so she books rides across the city to charm drivers and increase her score; Joan joins her neighbor's poker game in an effort to win an unusual prize; and John finally gets hearing aids but they aren't having the effect he was hoping for.

When Heather, Clementine and Jen offer to save Joan from the stress of preparing the Thanksgiving meal, the free time leaves Joan every more frazzled. Also, Greg has a boost of self-confidence after learning he has high levels of testosterone.

When Tim and Heather go to an expensive dinner to celebrate their anniversary, they are determined to finish every bite of their pricey 20-course meal. Also, Jen and Greg try to quickly potty-train Lark before her first day of preschool; Tyler gets jealous of the attention Clementine is getting at work; and Matt and Samantha team up for a “Middle Child Day” and go to a trapeze school.

When Heather tries to become Tyler's cool best friend, things take an awkward turn. Also, Jen and Greg get their first overnight away from Lark; Matt and Colleen regret returning their wedding presents for cash when they learn what John and Joan hid inside their gift; and Tim goes overboard when keeping a watchful eye on Samantha and her boyfriend.

When Jen and Greg hire Clementine as a part-time nanny for Lark and invite her to join them for dinner, the waitress mistakes Jen for Lark's grandmother. Also, Tyler's new girlfriend turns out to be Sophia's fourth grade teacher, John hires a questionable company to set up an escape room in his house, and Matt grows frustrated with Colleen when she blames a valet for stealing her lottery ticket.

The holiday spirit is alive, well and wildly different for each member of the Short family.

When Sophia asks Matt and Colleen about having children, an animated sequence featuring the whole family as farm animals reveals that they have been struggling to have a baby. Also, Jen and Greg's new neighbors aren't as nice as they initially seem; Heather interferes with Tim's hiring process at the office; and the whole family surprises Joan at her book reading, to her chagrin.

When Matt is in a hurry to get to the fertility clinic, each member of the family has a crisis that prevents him from getting there on time.

When Jen sings in Tyler's band, she gets caught up in the excitement and creates an awkward situation for him. Also, John and Greg decide to brew beer together, Matt donates one of his paintings to a silent auction for Tim's medical charity, and Heather becomes jealous of Joan's friendship with a classmate.

When Greg and Jen's crazy neighbors invite them to a party, Greg makes up a lie so they can get out of attending. Also, Matt and Colleen discover they need to give up some necessities to increase their chances of having a child; a delivery mix-up results in John and Joan accidentally receiving the fancy Japanese toilet Tim ordered for himself; and Sophia decides to shave her legs.

When Matt drives Greg to a job interview, they encounter a few bizarre obstacles that jeopardize getting him there on time. Also, with John's help, Tyler listens in on a therapy session between Clementine and Joan to see if she still has feelings for him; Tim bribes Samantha to attend online traffic school in his place; and Jen tries to convince Colleen and Tim to join her boycott of family get-togethers.

Jen and Greg decide to take turns dealing with her annoying parents when they come to visit. Also, when Tim and Heather chaperone Samantha's dance, Heather runs into an old flame; Colleen cashes in the many "love coupons" Matt has given her as gifts over the years; and Sophia digs up disturbing information when she investigates the family lineage.

When Sophia feels like she is no longer the cutest kid in the Short family, she tries frantically to regain her status. Also, Joan gives Jen a beautiful necklace, forgetting she already gave it to Heather for her Sweet 16, and now she has to get it back; Greg tries to fit in with his new young coworkers but takes things too far; and Colleen and Tim bond when he helps her administer the hormone injections for her IVF treatment.

When Heather tells Sophia she has to get rid of her stuffed animals, Sophia stages a musical with them to see if she can change her mother's mind. Also, Colleen babysits Lark, and Jen comes home to find her dolled up in Colleen's old pageant dress; Joan's bike is stolen from the driveway so she enlists Matt, Greg and Tim to join her in tracking it down; and Tyler and Clementine get John's help to sell their homemade beef jerky at the farmer's market.

Jen and Greg go to great lengths to find the perfect babysitter for Lark. Also, John becomes testy when shopping for a mattress and Joan realizes the unusual source of his aggravation; Heather learns information about Samantha's boyfriend that she isn't sure she should reveal; and Matt believes he may have a history with Colleen's sister after he meets her for the first time.

When Jen is offered a custom painting as payment from a hot new artist, she is thrilled until she sees the final product. Also, Sophia convinces Matt and Colleen to use her idea for a children's book but it isn't a new concept; Tyler and Clementine advertise their tiny house as a rental property; and John and Joan fall prey to a sleazy IRS scam.

The Short family's quirky history is revealed with stories of when Tim met Heather's family for the first time; when Jen and Greg bought their dream home; when Matt got sidetracked after he saw Colleen while waiting for a blind date; and John's last flight before retiring.

Heather asks Tyler and Tim to buy a bra for Samantha; Joan asks Jen to submit a recipe for the family cookbook, prompting Jen to steal one from her favorite restaurant; John gets Samantha and Sophia hooked on gambling.

Jen and Greg find out a surprising piece of news. Also, Sophia wants to get a second piercing in her ear, to the dismay of Heather and Tim; Colleen and Matt send out a video thank you message for their wedding gifts that irritates the family; and John takes a modeling job but is horrified when he finds out his image is used alongside a product for the elderly.

Tim and Heather plan a surprise birthday party for Samantha, but the night takes an unexpected turn when she doesn't come home alone. Also, Matt and Colleen learn their surrogate can no longer carry their baby; John and Joan decide to learn Spanish for their next adventure; and Jen and Greg have to find a way to keep their secret from the family.